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Foods (Basel, Switzerland) Dec 2023Red clover ( L.) is an important legume that is also known as a rich source of isoflavones, which are compounds with mild estrogenic activity. Therefore, this plant is...
Red clover ( L.) is an important legume that is also known as a rich source of isoflavones, which are compounds with mild estrogenic activity. Therefore, this plant is often used as a raw material in the production of dietary supplements recommended in menopause. Many factors can influence isoflavone content, but those genetically related are considered to be the most important. Therefore, the aim of this study was to evaluate the phytochemical profile of different plant parts of 30 red clover genotypes grouped according to ploidy and country of seed origin by analyzing the content of dominant isoflavones, total phenolic content (TPC) and antioxidant activity. It was found that there are significant differences in the examined traits among plant parts. Red clover leaves had the highest total isoflavone content, with biochanin A as the dominant compound, while flower extracts had the highest TPC and antioxidant activity. Diploid and tetraploid genotypes were significantly different concerning the content of daidzein, genistein, formononetin and TPC with higher quantities in tetraploid samples. On the other hand, seed origin was not a useful separating factor for the analyzed samples. The results of this research indicate that ploidy, as a previously poorly studied factor, could influence isoflavone content in red clover.
PubMed: 38201131
DOI: 10.3390/foods13010103 -
Applied Microbiology and Biotechnology Dec 2024This study describes the characterization of the recombinant GH3 aryl-β-glucosidase "GluLm" from Limosilactobacillus mucosae INIA P508, followed by its immobilization...
This study describes the characterization of the recombinant GH3 aryl-β-glucosidase "GluLm" from Limosilactobacillus mucosae INIA P508, followed by its immobilization on an agarose support with the aim of developing an efficient application to increase the availability and concentration of flavonoid and lignan aglycones in a vegetal beverage. In previous studies, heterologous GluLm-producing strains demonstrated a great capacity to deglycosylate flavonoids. Nevertheless, the physicochemical properties and substrate spectrum of the enzyme remained unknown up to now. A high production of purified GluLm was achieved (14 mg L). GluLm exhibited optimal activity at broad ranges of pH (5.0-8.0) and temperature (25-60°C), as well as high affinity (K of 0.10 mmol L) and specific constant (86554.0 mmol L s) against p-nitrophenyl-β-D-glucopyranoside. Similar to other GH3 β-glucosidases described in lactic acid bacteria, GluLm exhibited β-xylosidase, β-galactosidase, and β-fucosidase activities. However, this study has revealed for the first time that a GH3 β-glucosidase is capable to hydrolyze different families of glycosylated phenolics such as flavonoids and secoiridoids. Although it exhibited low thermal stability, immobilization of GluLm improved its thermostability and allowed the development of a beverage based on soybeans and flaxseed extract with high concentration of bioactive isoflavone (daidzein, genistein), lignan (secoisolariciresinol, pinoresinol, and matairesinol), and other flavonoid aglycones. KEY POINTS: • Limosilactobacillus mucosae INIA P508 GluLm was purified and biochemically characterized • Immobilized GluLm efficiently deglycosylated flavonoids and lignans from a vegetal beverage • A viable application to produce vegetal beverages with a high content of aglycones is described.
Topics: beta-Glucosidase; Polyphenols; Flavonoids; Phenols; Lignans
PubMed: 38189949
DOI: 10.1007/s00253-023-12956-9 -
Frontiers in Veterinary Science 2023In this study, the effects of quercetin and daidzein on egg quality, lipid metabolism, and cecal short-chain fatty acids (SCFAs) were compared in layers. Hyline brown...
In this study, the effects of quercetin and daidzein on egg quality, lipid metabolism, and cecal short-chain fatty acids (SCFAs) were compared in layers. Hyline brown layers at 385 days of age with a similar laying rate (81.36% ± 0.62%) and body weight (2.10 kg ± 0.04 kg) were randomly divided into three treatments, six replicates per treatment, and 20 layers per replicate. Layers in control, quercetin, and daidzein treatment were fed by a basal diet supplemented with 0 mg/kg, 500 mg/kg quercetin, and 30 mg/kg of daidzein for 10 weeks. Results showed that eggshell strength and albumen height in week 4, egg yolk diameter in week 10, and eggshell thickness and egg yolk height in weeks 4 and 10 were significantly increased in the quercetin treatment ( ≤ 0.05); contents of phospholipid (PL) and lecithin (LEC) in egg yolk and high-density lipoprotein (HDL) content in serum were significantly increased; however, contents of malondialdehyde (MDA), total cholesterol (TC), and triglyceride (TG) in egg yolk, contents of TC, TG, low-density lipoprotein (LDL), and very-low-density lipoprotein (VLDL) in serum, and contents of TC and TG in the liver were significantly decreased in the quercetin treatment ( ≤ 0.05); contents of isobutyric acid and valeric acid were significantly increased in the cecum of the quercetin treatment ( ≤ 0.05), compared with control. Moreover, egg yolk height in week 10 and eggshell thickness in weeks 4 and 10 were significantly increased in the daidzein treatment ( ≤ 0.05); contents of MDA, TC, and TG in egg yolk, TC, TG, and VLDL in serum, and TC and TG in liver were significantly decreased in the daidzein treatment ( ≤ 0.05); and HDL content was significantly increased in serum of the daidzein treatment ( ≤ 0.05) compared with control. However, daidzein did not affect SCFA content in the cecum. In conclusion, egg quality was improved by quercetin and daidzein by increasing the antioxidant ability of egg yolk and by regulating lipid metabolism in layers. Quercetin worked better than daidzein in improving egg quality under this experimental condition.
PubMed: 38188719
DOI: 10.3389/fvets.2023.1301542 -
Molecular Plant-microbe Interactions :... Apr 2024Soybean cyst nematode (, soybean cyst nematode [SCN]) disease adversely affects the yield of soybean and leads to billions of dollars in losses every year. To control...
Soybean cyst nematode (, soybean cyst nematode [SCN]) disease adversely affects the yield of soybean and leads to billions of dollars in losses every year. To control the disease, it is necessary to study the resistance genes of the plant and their mechanisms. Isoflavonoids are secondary metabolites of the phenylalanine pathway, and they are synthesized in soybean. They are essential in plant response to biotic and abiotic stresses. In this study, we reported that phenylalanine ammonia-lyase (PAL) genes s involved in isoflavonoid biosynthesis, can positively regulate soybean resistance to SCN. Our previous study demonstrated that the expression of genes in the resistant cultivar Huipizhi (HPZ) heidou are strongly induced by SCN. PAL is the rate-limiting enzyme that catalyzes the first step of phenylpropanoid metabolism, and it responds to biotic or abiotic stresses. Here, we demonstrate that the resistance of soybeans against SCN is suppressed by PAL inhibitor l-α-(aminooxy)-β-phenylpropionic acid (L-AOPP) treatment. Overexpression of eight genes caused diapause of nematodes in transgenic roots. In a petiole-feeding bioassay, we identified that two isoflavones, daidzein and genistein, could enhance resistance against SCN and suppress nematode development. This study thus reveals mediated resistance against SCN, information that has good application potential. The role of isoflavones in soybean resistance provides new information for the control of SCN. [Formula: see text] Copyright © 2024 The Author(s). This is an open access article distributed under the CC BY-NC-ND 4.0 International license.
Topics: Glycine max; Tylenchoidea; Plant Diseases; Animals; Phenylalanine Ammonia-Lyase; Disease Resistance; Gene Expression Regulation, Plant; Isoflavones; Plant Proteins; Plants, Genetically Modified
PubMed: 38171485
DOI: 10.1094/MPMI-09-23-0151-R -
Frontiers in Plant Science 2023The pathway for forming isoflavonoid skeletal structure is primarily restricted to the Leguminosae family. Subsequent decorations on the compound backbone by tailoring... (Review)
Review
The pathway for forming isoflavonoid skeletal structure is primarily restricted to the Leguminosae family. Subsequent decorations on the compound backbone by tailoring enzymes would change their biological and medicinal properties. is a leguminous plant, and as a traditional Chinese medicine its roots have been ascribed a number of pharmacological activities. Glycosylation and methylation are the main modifying processes in isoflavonoid metabolism in roots, resulting in the accumulation of unique glycosylated and methylated end isoflavonoid compounds. For instance, daidzein 8--glucoside (i.e., puerarin) and puerarin derivatives are produced only by the genus. Puerarin has been established as a clinical drug for curing cardiovascular diseases. To better understand the characteristic isoflavonoid metabolism in , this review attempts to summarize the research progress made with understanding the main glycosylation and methylation of isoflavonoids in and their biosynthetic enzymes.
PubMed: 38162309
DOI: 10.3389/fpls.2023.1330586 -
Journal of Enzyme Inhibition and... Dec 2024Transarterial chemoembolisation (TACE) is used for unresectable hepatocellular carcinoma (HCC) treatment, but TACE-induced hypoxia leads to poor prognosis. The...
Transarterial chemoembolisation (TACE) is used for unresectable hepatocellular carcinoma (HCC) treatment, but TACE-induced hypoxia leads to poor prognosis. The anti-cancer effects of soybean isoflavones daidzein derivatives 7,3',4'-trihydroxyisoflavone (734THIF) and 7,8,4'-trihydroxyisoflavone (784THIF) were evaluated under hypoxic microenvironments. Molecular docking of these isomers with cyclooxygenase-2 (COX-2) and vascular endothelial growth factor receptor 2 (VEGFR2) was assessed. About 40 μM of 734THIF and 784THIF have the best effect on inhibiting the proliferation of HepG2 cells under hypoxic conditions. At a concentration of 40 μM, 784THIF significantly inhibits COX-2 expression in pre-hypoxia conditions compared to 734THIF, with an inhibition rate of 67.73%. Additionally, 40 μM 784THIF downregulates the expression of hypoxic, inflammatory, and metastatic-related proteins, regulates oxidative stress, and inhibits the expression of anti-apoptotic proteins. The uptake by HepG2 confirmed higher 784THIF level and slower degradation characteristics under post- or pre-hypoxic conditions. In conclusion, our results showed that 784THIF had better anti-cancer effects and cellular uptake than 734THIF.
Topics: Humans; Carcinoma, Hepatocellular; Liver Neoplasms; Hep G2 Cells; Cyclooxygenase 2; Vascular Endothelial Growth Factor A; Molecular Docking Simulation; Hypoxia; Tumor Microenvironment
PubMed: 38153119
DOI: 10.1080/14756366.2023.2288806 -
Biochimica Et Biophysica Acta. Proteins... May 2024Methionine gamma lyase (MGL) is a bacterial and plant enzyme that catalyzes the conversion of methionine in methanthiol, 2-oxobutanoate and ammonia. The enzyme belongs... (Review)
Review
Methionine gamma lyase (MGL) is a bacterial and plant enzyme that catalyzes the conversion of methionine in methanthiol, 2-oxobutanoate and ammonia. The enzyme belongs to fold type I of the pyridoxal 5'-dependent family. The catalytic mechanism and the structure of wild type MGL and variants were determined in the presence of the natural substrate as well as of many sulfur-containing derivatives. Structure-function relationship studies were pivotal for MGL exploitation in the treatment of cancer, bacterial infections, and other diseases. MGL administration to cancer cells leads to methionine starvation, thus decreasing cells viability and increasing their vulnerability towards other drugs. In antibiotic therapy, MGL acts by transforming prodrugs in powerful drugs. Numerous strategies have been pursued for the delivering of MGL in vivo to prolong its bioavailability and decrease its immunogenicity. These include conjugation with polyethylene glycol and encapsulation in synthetic or natural vesicles, eventually decorated with tumor targeting molecules, such as the natural phytoestrogens daidzein and genistein. The scientific achievements in studying MGL structure, function and perspective therapeutic applications came from the efforts of many talented scientists, among which late Tatyana Demidkina to whom we dedicate this review.
Topics: Structure-Activity Relationship; Methionine; Racemethionine; Catalysis; Cell Survival
PubMed: 38147934
DOI: 10.1016/j.bbapap.2023.140991 -
Food Chemistry: X Dec 2023Distiller grains are the main by-products of production and are usually discarded, ignoring their abundant functional phytochemicals. The free and bound polyphenols...
Distiller grains are the main by-products of production and are usually discarded, ignoring their abundant functional phytochemicals. The free and bound polyphenols from distiller grains were extracted and their potential effect on modulating fecal microbiota was investigated using fecal fermentation. The results showed that 34 polyphenols were quantified from distiller grains. The antioxidant activity was positively correlated with quercetin, myricetin, epicatechin, and naringenin. The abundance of , , , , and butyrate-producing bacteria was enhanced by distiller's grain polyphenols by approximately 10.66-, 6.39-, 7.83-, 2.59-, and 7.74-fold, respectively. Moreover, the production of short-chain fatty acids (SCFAs), especially acetic, butyric, and propionic acid, was promoted (increased 1.99-, 1.71-, and 1.34-fold, respectively). Correlated analysis revealed quercetin, daidzein, and kaempferol as the key polyphenols by analyzing the effects on gut microbiota and SCFAs. This study could provide a reference for converting distiller grains into high-nutrient functional food ingredients and feeds.
PubMed: 38144726
DOI: 10.1016/j.fochx.2023.101001 -
Nutrients Dec 2023Phytoestrogens are non-steroidal plant compounds, which bind to α and β estrogen receptors, thereby causing specific effects. The best-known group of phytoestrogens... (Review)
Review
Phytoestrogens are non-steroidal plant compounds, which bind to α and β estrogen receptors, thereby causing specific effects. The best-known group of phytoestrogens are flavonoids, including isoflavonoids-genistein and daidzein. They play a role in the metabolism of bone tissue, improving its density and preventing bone loss, which contributes to reducing the risk of fractures. Vitamin D is found in the form of cholecalciferol (vitamin D3) and ergocalciferol (vitamin D2) and is traditionally recognized as a regulator of bone metabolism. The aim of this review was to evaluate the synergistic effect of isoflavonoids and vitamin D on bone mineral density (BMD). The MEDLINE (PubMed), Scopus and Cochrane databases were searched independently by two authors. The search strategy included controlled vocabulary and keywords. Reference publications did not provide consistent data regarding the synergistic effect of isoflavonoids on BMD. Some studies demonstrated a positive synergistic effect of these compounds, whereas in others, the authors did not observe any significant differences. Therefore, further research on the synergism of isoflavonoids and vitamin D may contribute to a significant progress in the prevention and treatment of osteoporosis.
Topics: Vitamin D; Bone Density; Phytoestrogens; Vitamins; Cholecalciferol
PubMed: 38140273
DOI: 10.3390/nu15245014 -
Genes Dec 2023Puerarin, a class of isoflavonoid compounds concentrated in the roots of , has antipyretic, sedative, and coronary blood-flow-increasing properties. Although the...
Puerarin, a class of isoflavonoid compounds concentrated in the roots of , has antipyretic, sedative, and coronary blood-flow-increasing properties. Although the biosynthetic pathways of puerarin have been investigated by previous researchers, studies focusing on the influence of different growth stages on the accumulation of metabolites in the puerarin pathway are not detailed, and it is still controversial at the last step of the 8--glycosylation reaction. In this study, we conducted a comprehensive analysis of the metabolomic and transcriptomic changes in var. thomsonii during two growing years, focusing on the vigorous growth and dormant stages, to elucidate the underlying mechanisms governing the changes in metabolite and gene expression within the puerarin biosynthesis pathway. In a comparison of the two growth stages in the two groups, puerarin and daidzin, the main downstream metabolites in the puerarin biosynthesis pathway, were found to accumulate mainly during the vigorous growth stage. We also identified 67 common differentially expressed genes in this pathway based on gene expression differences at different growth stages. Furthermore, we identified four candidate 8--GT genes that potentially contribute to the conversion of daidzein into puerarin and eight candidate 7--GT genes that may be involved in the conversion of daidzein into daidzin. A co-expression network analysis of important UGTs and HIDs along with daidzein and puerarin was conducted. Overall, our study contributes to the knowledge of puerarin biosynthesis and offers information about the stage at which the 8--glycosylation reaction occurs in biosynthesis. These findings provide valuable insights into the cultivation and quality enhancement of var. thomsonii.
Topics: Pueraria; Gene Expression Profiling; Transcriptome; Metabolomics
PubMed: 38137052
DOI: 10.3390/genes14122230